SaaStr AI London is Dec 1-2!! See You There!!

Helping, founding, funding, and growing B2B start-ups.  Making it a positive-sum game for everyone involved.  VC checks $500k-$4m @ SaaStrFund.com.  2x founder with nine figures of founder exits.

"Do or do not. There is no try."

Specialties: helping people grow and become their best.  Doing not the impossible, but the unlikely.  Never giving up.

Join 10,000 of us IRL at SaastrAnnual.com May 12-14 in SF Bay!!

FREE Weekly Workshops and Live AMAs, Sign up here -> https://www.saastr.com/workshop-wednesday/

SaaStrFund.com investments include:

- Co-led Series A in Salesloft ($2.3B exit)
- Co-led Seed in Pipedrive ($1.5B exit)
- Led Seed in Algolia ($2.3B)
- First VC in Talkdesk ($10B)
- Led Seed in Gorgias ($800m)
- Led Seed in Owner.com ($1B)
- First Investor in RevenueCat ($500m)
- First VC in Logikcull ($280m exit)
- Proud smaller investor in Greenhouse ($800m exit), Sqreen ($400m exit), Automile ($1B SEK exit), Opus Pro, Higgsfield.ai, and many others!
- and much more

The more customers you visit in person,
The more customers you close.
The more revenue you retain.
And the more they buy from you.

As true in 2025/2026 as it ever was.

Jason M. Lemkin

SaaStr AI 2026 is May 12-14 in SF Bay!! See You There!!

Folks are talking like 996 is something new.

I mean I worked in a services business early in my career.  And I worked 7:30-8 M-F, in the office most of the day Sat, and the morning on Sun.  Every dinner at my desk.

That's just the way it was.  

It's more that tech jobs from 2015-2024 were mentally hard in many cases, stressful, but really, not really "hard work" 

Not really.

Honestly, in many cases, at the 2021 demand peak, we barely worked.  Be honest.

Look how hard the folks in the ER work.  Or at the vet.  Or a lawyer working on an IPO or big deal.  Or someone operating their own restaurant, where it's do or die.

The work-from-home 25 hours a week, with a large team vibe ... it couldn't last.  It wasn't real. 

Sorry.

Do not take things personally
Do not take things personally
Do not take things personally
Do not take things personally

Hard for founders

At least try

There's so much advice out there, maybe here's my best advice of all:  

🙏Never Leave on Bad Terms🫂

Somehow, this became common in the 2021 era, and never went away.  Most folks, from the CRO + CMO level to the IC + SDR level:

- Just disappear and leave with no notice, just a Slack note or DM
- Write snarky things on LinkedIn / X
- In general, burn bridges on the way out, often without even realizing it

I get it. Layoffs are now omnipresent. Pressure is higher. The world has changed.  Maybe "loyalty" is a thing of a bygone era.  Maybe it never existed at all.  Maybe companies don't do what it takes to earn any loyalty anymore.  Probably they don't. 

But my advice is this:  imagine your goodbye lunch.

Remember those?  When everyone would take folks out when they gave their  notice?  Joke about the good times, and the less good times?  How everyone would thank them, including their managers?

Imagine that.  Leave that way.

Not because you need to, or own them anything.  You don't owe them anything.  But because you'll see them again.  Not next week.  But down the road.  

Most of us go from startup to startup, leader to leader.  Reference checks aren't what they once were, it's not that.  It's that someday, you'll see them again.  And you may wish ... you'd left on better terms.

Jason Lemkin

A quick summary of what you can and can’t replace with AI today:

- Outbound SDRs: you can replace most SDRs with AI today, possibly 100% … but you still need humans managing it and training it. Every day.

IF you truly go deep, train a platform, and orchestrate it >daily< you can replace most classic human email based SDRs with AI today. But you can’t just push a button. 

- Inbound BDRs: you can replace almost all of them with AI. If it’s well trained.

An AI should be able to qualify a lead faster and better than 95% of BDRs can. Today.

- Customer Support: you can replace 50% of your support team with AI today IF you invest. And deflect even more issues if the AI agent is well trained.

But again, only if you go deep, train a platform, orchestrate it >daily< AND create a very responsive human-in-the loop escalation strategy. 

- Marketing Managers: you probably don’t need half of them today at all.

Claude and ChatGPT as is can do a ton of marketing ops, and visual tools can create incredible collateral. Gamma can arm your team with better sales collateral than ever before. But again, you need a >lot< of orchestration.

- Customer Success. We need better AI platforms today, but we don’t need 60%+ of the CSMs we have today.

CSMs that don’t solve problems and just do QBRs without adding true value are not necessary in the age of AI. You can probably move on from them today.

- Account Execs: You still need 70% of them.

This should change in the next 24 months for in-bound, but we're not there yet. Field and in-person sales? Who knows.  

- Engineering: I’m not seeing that AI lets you reduce net headcount here at all. 

Instead, what I see overall is a 20%-40% productivity boost, net net. And far more for prototypes and proof-of-concept production.  

But it becomes an arms race. Everyone is more productive, software is shipping faster, so you need more great engineers than ever. It’s a cracked arms race in product development today.

Startups are hard

Personally:

- My cofounder walked out the door
- I spent all the money
- I had to sign at $750k note
- Our product failed at our top customer
- My VPS told my board I was incompetent
- My family didn't understand
- I went through recessions

Could have quit

Most SaaS AE interviews today, they're still looking for:

- $300k OTE
- Work from home
- No travel
- 100% in-bound
- Side hustles fine
- Strong SE support on product
- Sell their way
- Limited need to learn AI for real
- No prep required for interview or job

The world has changed

I have a seed investment I made years back now at $130m ARR now growing 40% and cash flow positive.  And all the VCs have checked out. 

They haven’t been mean about it.  Everyone is nice.  It’s just, one has their associate manage the investment now, hasn’t shown up in a long time.  

Another shows up once in a while, says Great Job.

This may sound like a criticism, but it isn’t.  It’s just a Sign Of The Times.  

Folks are just moving more quickly than ever to try to find the next Cursor or Harvey.

For founders, it’s good and less good.   The good part is you get left alone if growth is OK but not epic now, as long as you don’t need more money.  The less good part is the VCs disappear, and that can feel … not so good.

Buck up.  They are only investors.  Expect most to check out if you aren’t on a path to hypergrowth.  

And they may check back in once you achieve it again.

Founders never get “too senior” to do the actual work

They’ll always do it, Day 1 or Day 1000

This is often why we struggle with VPs that won’t.  And make mishires here.

We just assume they will.

The hardest part of sales is creating urgency

The rest is hard too, don't get me wrong

But really, 95 times out of 100, no one really needs to buy your product right now.  

Especially if it involves business process change.

I know it may not be what you want to hear

But the answer to how to get through tougher times is generally to work even harder

At least for a while

Your very, very best people are even better than you think they

Dig in and you’ll see they are doing even more great things than you realize

* Let them run
* Help them hire
* Let them make the mistake
* Wait to top them
* Thank them
* Pay them

Agentforce has delivered pretty darn impressive results for us -- for real. 

The >actual< data and live deep dive in post in comments.

AI agents do take work, but if you put in the time, the ROI can be massive.

Chair & CEO at Salesforce

SaaStr.ai is reaching new heights with #Agentforce. 📈

In just 30 days with our new Agentforce for Sales, the one and only Jason M. Lemkin:

• re-engaged approximately 3,000 ghosted leads
• achieved a remarkable 72% open rate
• closed deals from contacts that had been untouched for six months
• secured the highest response rate of any AI platform they tested

This goes beyond efficiency to driving revenue and reigniting old opportunities. The world of sales is changing, and #Agentforce is leading the charge. 

https://lnkd.in/eqEJmTEQ

Go upmarket, you scale faster, with less churn.  

And if you also stay downmarket too at the same time and keep serving those small customers well?

Then you end up with a product that is both super powerful.   And with unparalleled ease-of-use.

SaaStr AI Annual ’26 is May 12-14 in SF Bay!! See You There!!

Before $20,000,000 in ARR

Maybe even before $50,000,000 in ARR

Do not hire anyone with "strategist" in the first few lines of their LinkedIn bio

So far I've watched 3 VC seed deals this year where the founders just decided to keep the money for themselves and not build the product.

All were on SAFEs, and they took the position they owed investors nothing and that in fact they were not even investors. Just SAFE holders.

One eventually returned cash after keeping a large chunk for themselves.

Another hired an attorney who said plainly nothing was owed to the investors and the founders could pay themselves whatever they wanted.

I did not personally invest in these deals but I might have, they had a lot going for them (or so it seemed).

This is going to happen in the Age of AI. It's the flip side of so many things also exploding so quickly and growing at insane rates.

It's just a risk to be more aware of perhaps than in the past.

There are 2-3 days a quarter I feel like quitting

There are 2-3 days a quarter I'm sure it's isn't worth it

You're not alone

It "even" happens to me

I just don't tell anyone ;) 

You gotta push on.  That's always the answer when you have something.

Did you hire a good enough VP?

4 part test:

- who great did they hire in the first 60 days?
- did their #1 key metric improve?
- did they take part of the job off your plate?
- does the team believe?

If they don't pass the 4 part test, they aren't good enough

Caught up with an old colleague running sales at an AI company at $50m ARR.

🤵‍♀️They're building out their sales team now🧏‍♂️

The goal? 5 more humans, for a total of 8.

Yup. Just 8 total.

Too few? Probably. But they get 10,000+ leads a month, and want to focus.

A different world.

Engineering: sell what we have

Sales: build what I can sell

This, is The Enterprise

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